Controlled Release of Volatiles under Mild Reaction Conditions: From Nature to Everyday Products

Herrmann, Andreas

doi:10.1002/anie.200700264

Cited by 174 publications

(166 citation statements)

References 176 publications

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“…Equipping CB [8] with a photoresponsive ancillary guest may be regarded as a supramolecular approach to imparting photoresponsive properties to an otherwise photoinactive host, such that the complicated synthetic, covalent modification of host systems may be avoided. Our CB [8] catch-and-release strategy is a general approach to regulate the encapsulation of biologically important molecules, which may find applications in the fragrance industry 16 and other fields including photopharmacology 17 and optogenetics. 18 Furthermore, it may become useful for the development of artificial molecular devices which, in a fashion reminiscent to BR, can perform complex light-activated functions.…”

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confidence: 99%

Light-Regulated Molecular Trafficking in a Synthetic Water-Soluble Host

et al. 2016

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Abstract:The cucurbit [8]uril (CB[8])-mediated complexation of a dicationic azobenzene in water allows for the light-controlled encapsulation of a variety of second guest compounds, including amino acids, dyes and fragrance molecules. Such controlled guest sequestration inside the cavity of CB [8] enables the regulation of the thermally induced phase transition of poly(N-isopropylacrylamide) -which is not photosensitive -thus demonstrating the robustness and relevancy of the light-regulated CB[8] complexation.Light energy transduction is a fundamental phenomenon in the biosphere where living organisms are able to exploit sophisticated noncovalent constructs to transform light into kinetic and potential energy. For instance, visual transduction is initiated by the photoisomerization of retinal in the integral membrane protein Bacteriorhodopsin (BR), and results in the release of a proton to the extracellular environment.1 It is widely accepted that the exquisite control over the light-induced proton transfer is largely imparted by the delicate organization of the protein binding site. At a lower level of complexity, synthetic chemistry has enabled the production of artificial systems that, similarly to BR, can also bind and release protons and substantially larger species through a diversity of light-controlled processes.2 A variety of examples exist, including molecular tweezers, foldamers, cages and macrocycles.3 However, the design and synthesis of light-regulated containers that can operate in an aqueous environment remains a challenge, with only a few examples related to modified cyclodextrins.4 Such materials, provided they show reversible and tight binding to both neutral and charged species, could have significant impact in a variety of areas including photopharmacotherapy, drug delivery and encapsulation technologies.Here we describe a supramolecular container system exhibiting light-controlled encapsulation properties in water. Our multicomponent approach towards photoresponsive binding relies on an optimized design of its individual constituents and comprises the barrel-shaped molecule cucurbit [8] uril (CB[8])5 and a photoresponsive ancillary guest (Chart 1). Recently, we reported the controlled complexation of neutral guests in CB [8] aided by a series of aromatic bis(imidazolium) derivatives.6 Depending on their size, these salts can act as first guests for CB [8] enabling the encapsulation of relatively small second guests includ- †

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confidence: 99%

Light-Regulated Molecular Trafficking in a Synthetic Water-Soluble Host

et al. 2016

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“…Conjugated systems include a wide range of precursors, involving fragrance ingredients bound to carriers such as glycosides, carboxylates, carbamates, acetals, ketals and imines as well as inorganic esters, silanes, dendrimers and polymer based composites [8].…”

Section: Introductionmentioning

confidence: 99%

Organosilicon Fragrance Carriers

Ganicz

Kurjata

Perry

et al. 2015

Silicon

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Five different organosilicon carriers, with various molecular architectures -[(poly-(dimethylsiloxane-comethylsiloxane) (containing 61 % of [-SiMeHO-] monomeric units) (P), silicone resin (Q), tetramethyldisiloxane (M) tetramethylcyclotetrasiloxane (D) and tris (dimethylsilyl)methane [HC(SiMe 2 H) 3 , (T)] were covalently bonded with model fragrant systems, including 1-and 2-phenylethyl alcohol, acetophenone, 2-phenylpropionic aldehyde, geraniol, 2-phenyl-1-propyl alcohol, 2-octanone and octyl aldehyde in order to obtain novel controlled fragrance release systems. Hydrolytic release of the fragrances was studied under base (NaOH) and acid (HCl) catalysis. It has been shown that polymer carriers allow for a controlled slow release of the relevant fragrant ingredients from the conjugates, whereas the low molecular weight systems (M, D and T) more easily cleave off fragrant moieties.

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“…[12][13][14] The potential of using terpenoid glycoconjugates as slow-release aroma compounds in applications in which the glycosidic bond is cleaved either enzymatically or chemically has also been highlighted. [15] Whilst terpenoid glycosides exist as natural products, their levels in plant extracts are often limited. This has led to an increasing interest in synthesis.…”

Section: Introductionmentioning

confidence: 99%

Discovery of New Biocatalysts for the Glycosylation of Terpenoid Scaffolds

Caputi¹,

Lim²,

Bowles³

2008

Chemistry A European J

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The synthesis of terpenoid glycosides typically uses a chemical strategy since few biocatalysts have been identified that recognise these scaffolds. In this study, a platform of 107 recombinant glycosyltransferases (GTs), comprising the multigene family of small molecule GTs of Arabidopsis thaliana have been screened against a range of model terpenoid acceptors to identify those enzymes with high activity. Twenty-seven GTs are shown to glycosylate a diversity of mono-, sesqui- and diterpenes, such as geraniol, perillyl alcohol, artemisinic acid and retinoic acid. Certain enzymes showing substantial sequence similarity recognise terpenoids containing a primary alcohol, irrespective of the linear or cyclical structure of the scaffold; other GTs glycosylate scaffolds containing secondary and tertiary alcohols; the carboxyl group of other terpenoids also represents a feature that is recognized by GTs previously known to form glucose esters with many different compounds. These data underpin the rapid prediction of potential biocatalysts from GT sequence information. To explore the potential of GTs as biocatalysts, their use for the production of terpenoid glycosides was investigated by using a microbial-based whole-cell biotransformation system capable of regenerating the cofactor, UDP-glucose. A high cell density fermentation system was shown to produce several hundred milligrams of a model terpenoid, geranyl-glucoside. The activities of the GTs are discussed in relation to their substrate recognition and their utility in biotransformations as a complement or alternative to chemical synthesis.

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Controlled Release of Volatiles under Mild Reaction Conditions: From Nature to Everyday Products

Cited by 174 publications

References 176 publications

Light-Regulated Molecular Trafficking in a Synthetic Water-Soluble Host

Light-Regulated Molecular Trafficking in a Synthetic Water-Soluble Host

Organosilicon Fragrance Carriers

Discovery of New Biocatalysts for the Glycosylation of Terpenoid Scaffolds

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